Kate complains to Drew about a creepy employee named Earl, whom she thinks is crazy. Drew thinks Kate is paranoid until he finds that Earl is delusional and extremely unstable. When Drew fires Earl after he refuses to see the company psychiatrist, Earl threatens Drew and begins stalking him.
Mr. Bell promises Drew a promotion in exchange for training his nephew Blaine, who turns out to be a lazy, nepotistic pest. Kate mistakenly sells a giant bottle of extremely expensive perfume for much less than it's worth and turns to Drew for help. Meanwhile, Blaine becomes such a nuisance that Mimi and Drew call a truce and form an unholy alliance to force him out of the store.
The store closes early because of an ice storm and circumstances force Drew to miss his carpool with the Optimist Club. The Optimists get in an accident and a man dies. Drew believes divine intervention kept him from being in the accident and decides to contact his old pastor about becoming a minister.
Drew's hopes of a personal secretary are dashed when Mr. Bell gives the job to Mimi so he can hire Suzie as his own assistant. Drew and Mimi's continued bickering put both their jobs on the line and Drew is horrified when he discovers pictures that suggest Mimi is secretly in love with him.
Mrs. Louder is furious when she discovers Mr. Bell's affair with Suzie and forces him to fire her. Mr. Bell takes revenge by threatening to fire any member of management who is caught dating an employee. This means Drew and Lisa have to jump through hoops to keep seeing each other and avoid being caught, especially by an on-the-prowl Mimi.
Lisa encourages a reluctant Drew to move on and see other people like she has. He asks out his thrill-seeking barber Sioux, who manages to get Drew in a fight and, even worse, strikes up a friendship with Mimi. Just when Drew starts to wonder if he can keep up with Sioux, Lisa calls and tells him she's found a way they can date in public. But how can he tell Sioux and survive?
Drew is in hot water when Lisa and Kate find out he promised both of them the head personal shopper job. And just to send Drew farther over the edge, Mimi is also in the running for the position. Drew decides to be diplomatic and have all three of them shop for the store's most difficult customers. Whoever performs the best, wins the job.
Kate's mom takes Kate and the gang out to dinner for Kate's birthday. Kate avoids telling her mother she's dating anyone because her mom always disapproves of her boyfriends. Jay thinks Mrs. O'Brien is in a mental hospital but when Lewis lets the truth slip, Kate has to make up for it by inviting Jay to dinner at her mom's house. Just as Kate suspected, her mom worries Jay is on the rebound and tries to convince Kate that Drew is the right man for her.
The company motivational speaker encourages Drew to tell his bosses about his idea to use animal mascots in commercials for the store. Drew's idea is such a raging success, Mrs. Louder promotes him to head of promotions. Drew doesn't want to leave the personnel department but has to take the promotion. Unfortunately, Drew can't exactly handle the pressure of his new job: come up with fresh ideas each week or get fired.
Mimi and Drew find a secret memo that announces a Dutch company is planning to buy the store and they assume all the employees are going to be fired. Depressed about possibly losing his job, Drew and the gang visit a small business expo and eventually get the idea to brew and sell their own coffee-flavored beer.
Drew and Lisa's relationship gets rocky when all they do is argue everyday. On the work front, the Winfred-Louder staff sucks up to Drew because it's employee evaluation day. However, emotions run high when Lisa sees her less-than-complimentary evaluation early and is livid with Drew.
Drew is outraged when the company refuses to promote him to permanent manager and instead hires an Englishman named Nigel Wick. Wick turns out to be a very crooked character when he bribes Drew with the promise of the assistant manager job if he'll be Wick's "bad guy" when it comes to company cutbacks.
Lisa moves in with Drew and it really puts a strain on their relationship. Drew goes to great lengths to avoid going home at night while Kate, who thought Jay was going to propose, is confused and hurt when Jay says he is moving to Minnesota without her.
Drew runs into old high school bully Simon Tate (guest star Norm MacDonald) at the Warsaw. Simon apologizes for how he behaved as a teenager and seems to have changed his ways. Drew gives an out-of-work Simon a job at Winfred-Louder but he soon starts pushing everyone around just like in the old days.
Kate starts dating a new guy named Jack. He interviews for a position in the store and Drew is disturbed to find that Jack thinks he is the devil. Kate is sure Jack is just joking but soon finds out otherwise. When Kate tries to dump him, Jack claims she sold him her soul and says she can never leave him.
Drew is depressed after learning his high school band teacher, Ms. Blankenship, has died. He organizes the band to play a tribute performance for her and is furious when no one takes it seriously. When the gang questions Drew about it, he reveals that he lost his virginity to Ms. Blankenship. He considers the experience very special. However, Drew is dismayed to find out he was not the only male student seduced by the attractive music teacher.
Drew meets Bonnie (guest star Caroline Rhea) at the Warsaw and brings her home to see his brewery. Once she finds out he doesn't have a permit, she admits that she's a zoning inspector and has to report him. Drew organizes a party and sells maps to the location in order to give away the beer. Bonnie shows up at the party and threatens to arrest Drew and the gang for soliciting to sell alcohol. The party disbands but things get complicated when Drew and Bonnie sleep together after everyone leaves.
Drew is upset when Bonnie refuses to go out on dates with him in public. She always wants to stay over at his place and order take-out. Drew thinks Bonnie is concerned about his financial situation but he wants to do something special for her. Drew surprises Bonnie at her apartment with a gourmet meal, only to find out she's married.
Drew's hopes of a relaxing holiday weekend are crushed when Mr. Wick makes Drew in charge of Winfred-Louder's Thanksgiving Day parade. Crunched for time, Drew has to make a deal with Mimi that she can be the "snow queen" in the parade if her father's trucking company supplies the equipment for the floats. Unfortunately, Mr. Wick chooses someone else to be grand marshal and Mimi sabotages the parade.
Drew feels left out when popular salesman Dexter Roberts hang outs with all the other employees and embarrasses Drew in front of the whole store. Drew finds out Dexter is throwing a huge company party and only Drew and Mimi aren't invited. The two put aside their differences and decide to crash the party and ruin everyone's fun.
Drew inadvertently agrees to organize a wedding shower for his ex-girlfriend Lisa when he mistakenly believes the bride is an elderly employee also named Lisa. Lisa's fiancé Trent, according to Drew's new system that ranks employees by performance, is first in line to be fired from the store. Lisa thinks Drew is acting out of spite because he hasn't moved on but Drew insists it's because Trent is a poor employee. Drew talks with Trent and is unnerved when Trent has an epiphany and decides he wants to call off the wedding.